Abstract
Sea cucumbers or holothurians are marine invertebrates, belonging to the phylum Echinodermata (kingdom Animalia). In Asia, they are commonly used as food, while they are applied in traditional medicine as well. A wide range of secondary metabolites from these animals has been reported, but triterpene glycosides are the most predominant and most studied and are considered as valuable chemotaxonomic markers. With respect to this, the genus Holothuria is an important genus of sea cucumbers, given the high number and variety of triterpene glycosides previously reported. Holothuria triterpene glycosides are typically composed of a 3β-hydroxyholost-9(11)-ene aglycon and a glycosidic moiety comprised of one up to six sugar units, connected to position 3 of the sapogenin. In the past decade (2010–2020) as much as 63 saponins were identified for the first time in the Holothuria genus, of which 36 had not been reported before. Identification was mainly carried out by LC–MS (liquid chromatography—mass spectrometry) analysis, while also NMR (nuclear magnetic resonance) spectroscopy is often applied for structure elucidation. However, while carrying out a literature search on these compounds, various inconsistencies were observed. Therefore, this review intends to provide an overview of typical signals that can occur in NMR and MS data, accompanied with an extensive explanation of their interpretation, in order to facilitate any future research on identification/structure elucidation of Holothuria saponins. Moreover, the data published in the past decade were critically reviewed and various questionable results are discussed.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Change history
08 June 2022
A Correction to this paper has been published: https://doi.org/10.1007/s11101-022-09815-2
Abbreviations
- HPLC:
-
High performance liquid chromatography
- HRMS:
-
High resolution mass spectrometry
- LC-APCI-MS:
-
Liquid chromatography–atmospheric pressure chemical ionization–mass spectrometry
- LC–ESI–MS:
-
Liquid chromatography—electrospray ionization—mass spectrometry
- MALDI-FT-ICR MS:
-
Matrix-assisted laser desorption ionization-fourier transform-ion cyclotron resonance mass spectrometry
- MALDI-MS:
-
Matrix-assisted laser desorption ionization mass spectrometry
- MS:
-
Mass spectrometry
- MSI:
-
Mass spectrometry imaging
- NMR:
-
Nuclear magnetic resonance
- Q-ToF-MS:
-
Quadrupole time-of-flight mass spectrometry
References
Aminin DL, Menchinskaya ES, Pisliagin EA et al (2015) Anticancer activity of sea cucumber triterpene glycosides. Mar Drugs 13:1202–1223. https://doi.org/10.3390/md13031202
Anjaneyulu ASR, Raju KVS (1996) A new triterpene glycoside from the sea cucumber Holothuria atra off Mandapam coast. Indian J Chem 35B:810–814
Assawasuparerk K, Vanichviriyakit R, Chotwiwatthanakun C et al (2016) Scabraside D extracted from Holothuria scabra induces apoptosis and inhibits growth of human cholangiocarcinoma xenografts in mice. Asian Pac J Cancer Prev 17:511–517. https://doi.org/10.7314/APJCP.2016.17.2.511
Bahrami Y, Franco CMM (2015) Structure elucidation of new acetylated saponins, Lessoniosides A, B, C, D, and E, and non-acetylated saponins, Lessoniosides F and G, from the viscera of the sea cucumber holothuria lessoni. Mar Drugs 13:597–617. https://doi.org/10.3390/md13010597
Bahrami Y, Zhang W, Chataway T, Franco C (2014a) Structural elucidation of novel saponins in the sea cucumber Holothuria lessoni. Mar Drugs 12:4439–4473. https://doi.org/10.3390/md12084439
Bahrami Y, Zhang W, Franco C (2014b) Discovery of novel saponins from the viscera of the sea cucumber Holothuria lessoni. Mar Drugs 12:2633–2667. https://doi.org/10.3390/md12052633
Bahrami Y, Franco CMM, Benkendorff K (2016) Acetylated triterpene glycosides and their biological activity from holothuroidea reported in the past six decades. Mar Drugs 14:1–38. https://doi.org/10.3390/md14080147
Bahrami Y, Zhang W, Franco CMM (2018) Distribution of saponins in the sea cucumber holothuria lessoni; The body wall versus the viscera, and their biological activities. Mar Drugs 16(11):423. https://doi.org/10.3390/md16110423
Bondoc KGV, Lee H, Cruz LJ et al (2013) Chemical fingerprinting and phylogenetic mapping of saponin congeners from three tropical holothurian sea cucumbers. Comp Biochem Physiol B Biochem Mol Biol 166:182–193. https://doi.org/10.1016/j.cbpb.2013.09.002
Caulier G, Van DS, Gerbaux P et al (2011) Review of saponin diversity in sea cucumbers belonging to the family Holothuriidae. SPC Beche-De-Mer Inf Bull 31:48–54
Caulier G, Flammang P, Gerbaux P, Eeckhaut I (2013a) When a repellent becomes an attractant: harmful saponins are kairomones attracting the symbiotic Harlequin crab. Sci Rep 3:1–5. https://doi.org/10.1038/srep02639
Caulier G, Flammang P, Rakotorisoa P, et al (2013b) Preservation of the bioactive saponins of Holothuria scabra through the processing of trepang. Cah Biol Mar 54:685–690.
Caulier G, Mezali K, Soualili DL et al (2016) Chemical characterization of saponins contained in the body wall and the Cuvierian tubules of the sea cucumber Holothuria (Platyperona) sanctori (Delle Chiaje, 1823). Biochem Syst Ecol 68:119–127. https://doi.org/10.1016/j.bse.2016.06.005
El Barky AR, Hussein SA, Alm-Eldeen AA et al (2016) Anti-diabetic activity of Holothuria thomasi saponin. Biomed Pharmacother 84:1472–1487. https://doi.org/10.1016/j.biopha.2016.10.002
Elbandy M, Rho JR, Afifi R (2014) Analysis of saponins as bioactive zoochemicals from the marine functional food sea cucumber Bohadschia cousteaui. Eur Food Res Technol 238:937–955. https://doi.org/10.1007/s00217-014-2171-6
Elyakov GB, Stonik VA, Levina EV et al (1973) Glycosides of marine invertebrates-I. A comparative study of the glycoside fractions of pacific sea cucumbers. Comp Biochem Physiol Part B Biochem 44:325–336. https://doi.org/10.1016/0305-0491(73)90005-9
Elyakov GB, Kuznetsova TA, Stonik VA et al (1975) Glycosides of marine invertebrates-IV. A comparative study of the glycosides from Cuban sublittoral holothurians. Comp Biochem Physiol Part B Biochem 52:413–417. https://doi.org/10.1016/0305-0491(75)90154-6
Elyakov GB, Kalinovskaya NI, Kalinovskii AI et al (1982) Glycosides of marine invertebrates XIII. New holothurinogenins of holothurin B1 from Holothuria floridana. Chem Nat Compd 18:298–302. https://doi.org/10.1007/BF00580455
Friess SL, Durant RC, Chanley JD (1968) Further studies on biological actions of steroidal saponins produced by poisonous echinoderms. Toxicon 6:81–92
Grauso L, Yegdaneh A, Sharifi M et al (2019) Molecular networking-based analysis of cytotoxic saponins from sea cucumber holothuria atra. Mar Drugs 17:1–13. https://doi.org/10.3390/md17020086
Hal DM, Eltamany EE, Abdelhameed RFA et al (2020) Genus Holothuria an imminent source of diverse chemical entities: a review. Rec Pharm Biomed Sci 4:46–67. https://doi.org/10.21608/RPBS.2020.32514.1067
Han H, Yi YH, Li L et al (2007) A new triterpene glycoside from sea cucumber Holothuria leucospilota. Chinese Chem Lett 18:161–164. https://doi.org/10.1016/j.cclet.2006.12.027
Han H, Yi YH, Liu BS et al (2008) Leucospilotaside C, a new sulfated triterpene glycoside from sea cucumber Holothuria leucospilota. Chin Chem Lett 19:1462–1464. https://doi.org/10.1016/j.cclet.2008.09.051
Han H, Yi Y, Xu Q et al (2009a) Two new cytotoxic triterpene glycosides from the sea cucumber Holothuria scabra. Planta Med 75:1608–1612. https://doi.org/10.1055/s-0029-1185865
Han H, Yi YH, Li L et al (2009b) Triterpene glycosides from sea cucumber Holothuria leucospilota. Chin J Nat Med 7:346–350. https://doi.org/10.3724/SP.J.1009.2009.00346
Han H, Yi YH, Li L et al (2009c) Antifungal active triterpene glycosides from sea cucumber Holothuria scabra. Yao Xue Xue Bao 44(6):620–624
Han H, Zhang W, Yi YH et al (2010) A novel sulfated holostane glycoside from sea cucumber Holothuria leucospilota. Chem Biodivers 7:1764–1769. https://doi.org/10.1002/cbdv.200900094
Han H, Li L, Yi Y et al (2012) Triterpene glycosides from sea cucumber Holothuria scabra with cytotoxic activity. Chinese Herb Med 4:183–188. https://doi.org/10.3969/j.issn.1674-6384.2012.03.002
Hoang L, Le Thi V, Tran Thi Hong H et al (2020) Triterpene glycosides from the Vietnamese sea cucumber Holothuria edulis. Nat Prod Res 34:1061–1067. https://doi.org/10.1080/14786419.2018.1548451
Honey-Escandón M, Arreguín-Espinosa R, Solís-Marín FA, Samyn Y (2015) Biological and taxonomic perspective of triterpenoid glycosides of sea cucumbers of the family Holothuriidae (Echinodermata, Holothuroidea). Comp Biochem Phys B 180:16–39. https://doi.org/10.1016/j.cbpb.2014.09.007
Hostettmann K, Marston A (1995) Occurrence and distribution. Saponins (chemistry and pharmacology of natural products. Cambridge University Press, Cambridge, pp 18–121
Ivanova NS, Smetanina OF, Kuznetsova T a, Eastern F (1984) Glycosides of marine invertebrates. XXVI. Holothurin A from the Pacific Ocean holothurian, Holothuria squamifera. Isolation of native aglycon. Khimiya Prir Soedin, pp 448–451.
Jattujan P, Chalorak P, Siangcham T et al (2018) Holothuria scabra extracts possess anti-oxidant activity and promote stress resistance and lifespan extension in Caenorhabditis elegans. Exp Gerontol 110:158–171. https://doi.org/10.1016/j.exger.2018.06.006
Kalinin VI, V.A. S, (1983) Glycosides of marine invertebrates. Structure of holothurin A2 from the holothurian Holothuria edulis. Khimiya Prir Soedin 2:215–219
Kalinin VI, Silchenko AS, Avilov SA et al (2005) Sea cucumbers triterpene glycosides, the recent progress in structural elucidation and chemotaxonomy. Phytochem Rev 4:221–236. https://doi.org/10.1007/s11101-005-1354-y
Kalinin VI, Aminin DL, Avilov SA et al (2008) Triterpene glycosides from sea cucucmbers (holothurioidea, echinodermata). Biological activities and functions. Stud Nat Prod Chem 35:135–196. https://doi.org/10.1016/S1572-5995(08)80006-3
Kamyab E, Goebeler N, Kellermann MY et al (2020) Anti-fouling effects of saponin-containing crude extracts from tropical Indo-Pacific sea cucumbers. Mar Drugs 18(4):181. https://doi.org/10.3390/md18040181
Kim SK, Himaya SWA (2012) Triterpene glycosides from Sea cucumbers and their biological activities. Adv Food Nutr Res 65:297–319. https://doi.org/10.1016/B978-0-12-416003-3.00020-2
Kitagawa I, Nishino T, Kyogoku Y (1979) Structure of holothurin A a biologically active triterpene-oligoglycoside from the sea cucumber holothuria leucospilota brandt. Tetrahedron Lett 20(16):1419–1422. https://doi.org/10.1016/S0040-4039(01)86166-9
Kitagawa I, Nishino T, Kobayashi M, Kyogoku Y (1981) Marine natural products. VIII. Bioactive triterpene-oligoglycosides from the sea cucumber Holothuria leucospilota Brandt (2). Structure of holothurin A. Chem Pharm Bull 29:1951–1956
Kitagawa I, Kobayashi M, Son BW et al (1989) Marine natural products. XIX. Pervicosides A, B, and C, lanostane-type triterpene-oligoglycoside sulfates from the sea cucumber Holothuria pervicax. Chem Pharm Bull 37:1230–1234
Kobayashi M, Hori M, Kan K et al (1991) Marine natural products. XXVII. Distribution of lanostane-type triterpene oligoglycosides in ten kinds of Okinawan sea cucumbers. Chem Pharm Bull 39:2282–2287
Kuznetsova TA, Anisimov MM, Popov AM et al (1982a) A comparative study in vitro of physiological activity of triterpene glycosides of marine invertebrates of echinoderm type. Comp Biochem Physiol Part C Comp 73:41–43. https://doi.org/10.1016/0306-4492(82)90165-4
Kuznetsova TA, Kalinovskaya NI, Kalinovskii AI, et al (1982b) Glycosides of marine invertebrates. XIV. Structure of holoturin B1 from the holothurian Holothuria floridana. Khimiya Prir Soedin, pp 482–484.
Li M, Miao ZH, Chen Z et al (2010) Echinoside A, a new marine-derived anticancer saponin, targets topoisomerase2α by unique interference with its DNA binding and catalytic cycle. Ann Oncol 21:597–607. https://doi.org/10.1093/annonc/mdp335
Melek FR, Tadros MM, Yousif F et al (2012) Screening of marine extracts for schistosomicidal activity in vitro. Isolation of the triterpene glycosides echinosides A and B with potential activity from the Sea Cucumbers Actinopyga echinites and Holothuria polii. Pharm Biol 50:490–496. https://doi.org/10.3109/13880209.2011.615842
Mert Ozupek N, Cavas L (2017) Triterpene glycosides associated antifouling activity from Holothuria tubulosa and H. polii. Reg Stud Mar Sci 13:32–41. https://doi.org/10.1016/j.rsma.2017.04.003
Miller AK, Kerr AM, Paulay G et al (2017) Molecular phylogeny of extant Holothuroidea (Echinodermata). Mol Phylogenet Evol 111:110–131. https://doi.org/10.1016/j.ympev.2017.02.014
Minh CV, Kiem PV, Huong LM al et al (2005) Triterpene-glycosides of lanostane type with cytotoxic activity from Holothuria martensii. J Chem-NY 43:768–772
Mitu SA, Bose U, Suwansa-ard S et al (2017) Evidence for a saponin biosynthesis pathway in the body wall of the commercially significant sea cucumber Holothuria scabra. Mar Drugs 15(11):349. https://doi.org/10.3390/md15110349
Nguyen HD, Van Thanh N, Van Kiem P et al (2007) Two new triterpene glycosides from the Vietnamese sea cucumber Holothuria scabra. Arch Pharm Res 30:1387–1391. https://doi.org/10.1007/bf02977361
Nursid M, Marraskuranto E, Chasanah E (2019) Cytotoxicity and apoptosis induction of sea cucumber Holothuria atra extracts. Pharmacognosy Res 11:41–46. https://doi.org/10.4103/pr.pr_3_18
Oleinikova GK, Kuznetsova TA, Ivanova NS, et al (1982a) Glycosides of marine invertebrates XV. A new triterpene glycoside—holothurin A1-from caribbean holothurians of the family holothuriidae. Khimiya Prir Soedin, pp 464–469.
Oleinikova GK, Kuznetsova TA, Rovnykh N V, et al (1982b) Glycosides of marine invertebrates. XVIII. Holothurin A2 from the caribbean holothurian Holothuria floridana. Khimiya Prir Soedin, pp 527–528.
Oleinikova GK, Kuznetsova TA (1986) Glycosides of the holothurian Holothuria atra. Chem Nat Compd 22:617. https://doi.org/10.1007/BF00599287
Omran NE, Salem HK, Eissa SH et al (2020) Chemotaxonomic study of the most abundant Egyptian sea-cucumbers using ultra-performance liquid chromatography (UPLC) coupled to high-resolution mass spectrometry (HRMS). Chemoecology 30:35–48. https://doi.org/10.1007/s00049-019-00296-y
Radhika P, Anjaneyulu V, Subba Rao PV et al (2002) Chemical examination of the echinoderms of Indian Ocean: the triterpene glycosides of the sea cucumbers: Holothuria nobilis, Bohadschia aff. tenuissima and Actinopyga mauritana from Lakshadweep, Andaman and Nicobar Islands. Indian J Chem B 41:1276–1282
Rodriguez J, Riguera R (1989) Lefevreiosides: four novel triterpenoid glycosides from the sea cucumber Cucumaria lefevrei. J Chem Res 11:342–343
Rodriguez J, Castro R, Riguera R (1991) Holothurinosides: new antitumour non sulphated triterpenoid glycosides from the sea cucumber Holothuria forskalii. Tetrahedron 47:4753–4762. https://doi.org/10.1016/S0040-4020(01)86479-6
Sangpairoj K, Chaithirayanon K, Vivithanaporn P et al (2016) Extract of the sea cucumber, Holothuria scabra, induces apoptosis in human glioblastoma cell lines. Funct Foods Heal Dis 6:452. https://doi.org/10.31989/ffhd.v6i7.264
Shahinozzaman M, Ishii T, Takano R et al (2018) Cytotoxic desulfated saponin from Holothuria atra predicted to have high binding affinity to the oncogenic kinase PAK1: a combined in vitro and in silico study. Sci Pharm 86:1–13. https://doi.org/10.3390/scipharm86030032
Shushizadeh M, Mohammadi Pour P, Mahdieh M, Yegdaneh A (2019) Phytochemical analysis of Holothuria leucospilota, a sea cucumber from Persian Gulf. Res Pharm Sci 14:432–440. https://doi.org/10.4103/1735-5362.268204
Silchenko AS, Stonik VA, Avilov SA et al (2005) Holothurins B2, B3, and B4, new triterpene glycosides from Mediterranean sea cucumbers of the genus Holothuria. J Nat Prod 68:564–567. https://doi.org/10.1021/np049631n
Sroyraya M, Kaewphalug W, Anantachoke N et al (2018) Saponins enriched in the epidermal layer of Holothuria leucospilota body wall. Microsc Res Tech 81:1182–1190. https://doi.org/10.1002/jemt.23115
Stonik VA (1986) Some terpenoid and steroid derivatives from echinoderms and sponges. Pure Appl Chem 58:423–436. https://doi.org/10.1351/pac198658030423
Stonik VA, Kalinin VI, Avilov SA (1999) Toxins from sea cucumber (Holothuroids): chemical structures, properties, taxonomic distribution, biosynthesis and evaluation. J Nat Toxins 8:235–248
Sun P, Yi YH, Li L et al (2006) 17-deydroxyholothurin A, a new sulfated triterpene glycoside from sea cucumber Holothuria impatie. Chin Chem Lett 17:1454–1456
Sun P, Liu BS, Yi YH et al (2007) A new cytotoxic lanostane-type triterpene glycoside from the sea cucumber Holothuria impatiens. Chem Biodivers 4:450–457. https://doi.org/10.1002/cbdv.200790037
Sun G, Li L, Yi Y et al (2008a) Two new cytotoxic nonsulfated pentasaccharide holostane ( = 20-hydroxylanostan-18-oic acid -gamma-lactone ) glycosides from the sea cucumber Holothuria grisea. Helv Chim Acta 91:1453–1460
Sun P, Yi YH, Li L, Tang HF (2008b) Studies on chemical constituents from the sea cucumber Holothuria impatiens. Zhongguo Haiyang Yaowu 27:1–7
Thanh NV, Dang NH, Kiem PV et al (2006) A new triterpene glycoside from the sea cucumber Holothuria Scabra collected in Vietnam. ASEAN J Sci Technol Dev 23:253–259. https://doi.org/10.3125/asean.v23i4.986
Van Dyck S, Gerbaux P, Flammang P (2009) Elucidation of molecular diversity and body distribution of saponins in the sea cucumber Holothuria forskali (Echinodermata) by mass spectrometry. Comp Biochem Physiol B Biochem Mol Biol 152:124–134. https://doi.org/10.1016/j.cbpb.2008.10.011
Van Dyck S, Flammang P, Meriaux C et al (2010a) Localization of secondary metabolites in marine invertebrates: Contribution of MALDI MSI for the study of saponins in Cuvierian tubules of H. forskali. PLoS ONE. https://doi.org/10.1371/journal.pone.0013923
Van Dyck S, Gerbaux P, Flammang P (2010b) Qualitative and quantitative saponin contents in five sea cucumbers from the Indian ocean. Mar Drugs 8:173–189. https://doi.org/10.3390/md8010173
Van Dyck S, Caulier G, Todesco M et al (2011) The triterpene glycosides of Holothuria forskali: usefulness and efficiency as a chemical defense mechanism against predatory fish. J Exp Biol 214:1347–1356. https://doi.org/10.1242/jeb.050930
Wang J, Han H, Chen X et al (2014) Cytotoxic and apoptosis-inducing activity of triterpene glycosides from Holothuria scabra and Cucumaria frondosa against HepG2 Cells. Mar Drugs 12:4274–4290. https://doi.org/10.3390/md12084274
Weng Y, Yi Y, Li L et al (2007) Three triterpene glycosides from Holothuria arenicola. Zhongguo Tianran Yaowu 5:96–100
World Register of Marine Species (WORMS) (2021) Holothuriidae Burmeister, 1837. http://www.marinespecies.org/aphia.php?p=taxdetails&id=731943. Accessed 29 Jan 2021
Wu J, Yi Y, Tang H et al (2006a) Structure and cytotoxicity of a new lanostane-type triterpene glycoside from the sea cucumber Holothuria hilla. Chem Biodivers 3:1249–1254
Wu J, Yi Y, Zou ZR et al (2006b) Two new triterpene glycosides from sea cucumber Holothuria nobilis. Zhongcaoyao 37:497–500
Wu J, Yi YH, Tang HF et al (2006c) Nobilisides A-C, three new triterpene glycosides from the sea cucumber Holothuria nobilis. Planta Med 72:932–935. https://doi.org/10.1055/s-2006-931603
Wu J, Yi YH, Tang HF et al (2007) Hillasides A and B, two new cytotoxic triterpene glycosides from the sea cucumber Holothuria hilla lesson. J Asian Nat Prod Res 9:609–615. https://doi.org/10.1080/10286020600882676
Wu J, Zhang JJ, Zhu KQ, et al (2009) Anti-tumor compound nobiliside E separated from Thelenota ananas (patent CN 101463066, Faming Zhuanli Shenqing).
Yu S, Ye X, Huang H et al (2015) Bioactive sulfated saponins from sea cucumber Holothuria moebii. Planta Med 81:152–159. https://doi.org/10.1055/s-0034-1383404
Yuan W-H, Yi Y-H, Xue M et al (2008a) Two antifungal active triterpene glycosides from sea cucumber Holothuria (Microthele) axiloga. Chin J Nat Med 6:105–108. https://doi.org/10.1016/s1875-5364(09)60010-8
Yuan WH, Yi YH, Li L et al (2008b) Two triterpene glycosides from the sea cucumber Bohadschia marmorata Jaeger. Chin Chem Lett 19:457–460. https://doi.org/10.1016/j.cclet.2008.01.026
Yuan WH, Yi YH, Tan RX et al (2009a) Antifungal triterpene glycosides from the sea cucumber Holothuria (Microthele) axiloga. Planta Med 75:647–653. https://doi.org/10.1055/s-0029-1185381
Yuan WH, Yi YH, Tang HF et al (2009b) Antifungal triterpene glycosides from the sea cucumber Bohadschia marmorata. Planta Med 75:168–173. https://doi.org/10.1055/s-0028-1088348
Zhang JJ (2011) Extraction, isolation, and structure elucidation of two new triterpene glycosides from sea cucumber Holothuria nobilis. Zhong Cao Yao 8:1467–1472
Zhang JJ, Zhu KQ (2017) A novel antitumor compound nobiliside D isolated from sea cucumber (Holothuria nobilis Selenka). Exp Ther Med 14:1653–1658. https://doi.org/10.3892/etm.2017.4656
Zhang SY, Yi YH, Tang HF (2006) Bioactive triterpene glycosides from the sea cucumber Holothuria fuscocinerea. J Nat Prod 69:1492–1495. https://doi.org/10.1021/np060106t
Zhang JJ, Dai JB, Chen LL, Ding PY, Wu J (2008) Screening of bioactive constituents from sea cucumber Holothuria nobilis using conidia of Pyricularia oryzae. J Chin Med Mater 31(7):1001–1003
Zhang JJ, Zhu QK, Wu J, Zhang HW (2015) New cytotoxic triterpene glycoside from the east China sea cucumber Holothuria nobilis. Nat Prod Commun 10:247–248. https://doi.org/10.1177/1934578x1501000207
Acknowledgements
The Indonesia Endowment Fund for Education/Lembaga Pengelola Dana Pendidikan (LPDP) and Indonesian Ministry of Research, Technology and Higher Education (RISTEKDIKTI) are acknowledged for the financial support of the research of Yunita Eka Puspitasari. Dr. Tuo Li from the Institute of Synthetic Biology, Shenzhen Institutes of Advanced Technology, Chinese Academy of Sciences is gratefully thanked for helping with the interpretation of various publications written in Chinese.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors declare no conflict of interest.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Puspitasari, Y.E., De Bruyne, T., Foubert, K. et al. Holothuria triterpene glycosides: a comprehensive guide for their structure elucidation and critical appraisal of reported compounds. Phytochem Rev 21, 1315–1358 (2022). https://doi.org/10.1007/s11101-021-09783-z
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11101-021-09783-z